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Unprotected Xylose‐Derived Nitrone in Stereodivergent Synthesis of 4‐Hydroxypiperidine Enantiomers: Weak Lewis Acid Induced Alteration of Stereochemistry in 1,3‐Dipolar Cycloaddition
Author(s) -
Rowicki Tomasz,
Malinowski Maciej,
Gryszel Maciej,
Czerwińska Karolina,
Madura Izabela,
MironiukPuchalska Ewa,
KoszytkowskaStawińska Mariola,
Sas Wojciech
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403410
Subject(s) - chemistry , nitrone , cycloaddition , lewis acids and bases , enantiomer , bicyclic molecule , chiral lewis acid , piperidine , stereochemistry , 1,3 dipolar cycloaddition , intramolecular force , enantioselective synthesis , enantiomeric excess , organic chemistry , catalysis
A one‐pot, two‐step synthesis of chiral 7‐oxa‐1‐azabicyclo[2.2.1]heptane derivatives from unprotected D ‐xylose was achieved by an intramolecular 1,3‐dipolar cycloaddition of the N ‐(γ‐alkenyl)‐substituted nitrone intermediate. The stereochemical course of the cycloaddition was altered by the addition of an achiral Lewis acid. The bicyclic byproducts were employed in a concise synthesis of two new enantiomeric piperidine‐type iminosugars.